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Mepirizole

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1 USDMF

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Chemistry

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Also known as: Mepirizole, 18694-40-1, Mebron, Methopyrimazole, 4-methoxy-2-(5-methoxy-3-methyl-1h-pyrazol-1-yl)-6-methylpyrimidine, Mepirizol

Molecular Formula

C₁₁H₁₄N₄O₂

Molecular Weight

234.25 g/mol

InChI Key

RHAXSHUQNIEUEY-UHFFFAOYSA-N

FDA UNII

3B46O2FH8I

4-Methoxy-2-(5-methoxy-3-methylpyrazol-1-yl)-6-methylpyrimidine. A pyrimidinyl pyrazole with antipyretic, analgesic, and anti-inflammatory activity.

1 2D Structure

Mepirizole

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-methoxy-2-(5-methoxy-3-methylpyrazol-1-yl)-6-methylpyrimidine

2.1.2 InChI

InChI=1S/C11H14N4O2/c1-7-5-9(16-3)13-11(12-7)15-10(17-4)6-8(2)14-15/h5-6H,1-4H3

2.1.3 InChI Key

RHAXSHUQNIEUEY-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CC(=NC(=N1)N2C(=CC(=N2)C)OC)OC

2.2 Other Identifiers

2.2.1 UNII

3B46O2FH8I

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Mepirizole

2. Methopyrimazole

2.3.2 Depositor-Supplied Synonyms

1. Mepirizole

2. 18694-40-1

3. Mebron

4. Methopyrimazole

5. 4-methoxy-2-(5-methoxy-3-methyl-1h-pyrazol-1-yl)-6-methylpyrimidine

6. Mepirizol

7. Da-398

8. Epirizolum [inn-latin]

9. 4-methoxy-2-(5-methoxy-3-methylpyrazol-1-yl)-6-methylpyrimidine

10. Pyrimidine, 4-methoxy-2-(5-methoxy-3-methyl-1h-pyrazol-1-yl)-6-methyl-

11. Mls000028844

12. 3b46o2fh8i

13. 1-(4-methoxy-6-methyl-2-pyrimidinyl)-3-methyl-5-methoxypyrazole

14. 2-(3-methoxy-5-methylpyrazol-2-yl)-4-methoxy-6-methylpyrimidine

15. 2-(3-methyl-5-methoxy-1-pyrazolyl)-4-methoxy-6-methylpyrimidine

16. Ncgc00016737-01

17. Smr000058715

18. 4-methoxy-2-(5-methoxy-3-methylpyrazol-1-yl)-6-methylpyrimidin

19. Cas-18694-40-1

20. Dsstox_cid_25422

21. Dsstox_rid_80869

22. Dsstox_gsid_45422

23. Mepirizol [german]

24. Epirizolum

25. Epirizol

26. Epirizol [inn-spanish]

27. Pyrimidine,4-methoxy-2-(5-methoxy-3-methyl-1h-pyrazol-1-yl)-6-methyl-

28. Epirizole [usan:inn:jan]

29. Einecs 242-507-1

30. Brn 0751084

31. Unii-3b46o2fh8i

32. Prestwick_201

33. Mebron (tn)

34. Epirizole [inn]

35. Epirizole [jan]

36. Opera_id_598

37. Epirizole [mi]

38. Epirizole [usan]

39. Prestwick0_000032

40. Prestwick1_000032

41. Prestwick2_000032

42. Prestwick3_000032

43. Epirizole [mart.]

44. 4-methoxy-2-(5-methoxy-3-methylpyrazol-1-yl)-6-methylpyrimidin [german]

45. Epirizole (jp17/usan)

46. Epirizole [who-dd]

47. Schembl23765

48. Bspbio_000123

49. 5-25-18-00012 (beilstein Handbook Reference)

50. Mls001148256

51. Mls001424179

52. Spbio_002044

53. Mepirizole, Analytical Standard

54. Bpbio1_000137

55. Chembl1411693

56. Dtxsid4045422

57. Chebi:31545

58. Zinc57412

59. Hms1568g05

60. Hms2052a07

61. Hms2095g05

62. Hms2232e23

63. Hms3370d19

64. Hms3394a07

65. Hms3712g05

66. Tox21_110584

67. Pyrimidine, 4-methoxy-2-(5-methoxy-3-methylpyrazol-1-yl)-6-methyl-

68. Akos016000700

69. Tox21_110584_1

70. Ccg-101087

71. Db08991

72. Nc00337

73. Ncgc00016737-02

74. Ncgc00016737-04

75. Hy-103595

76. Cs-0022015

77. Ft-0637738

78. Mls000028844-02

79. D01394

80. 694m401

81. Sr-01000721915

82. J-012020

83. Q5383219

84. Sr-01000721915-3

85. Brd-k39339537-001-03-8

86. 2-(3-methyl-5-methoxy-1-pyrazolyl)-4-methoxy-6-methyl-pyrimidine

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₁₄N₄O₂
Molecular Weight	234.25 g/mol
XLogP3	1.3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Exact Mass	234.11167570 g/mol
Monoisotopic Mass	234.11167570 g/mol
Topological Polar Surface Area	62.1 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	254
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anti-Inflammatory Agents, Non-Steroidal

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

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